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Volumn 53, Issue 28, 2012, Pages 3581-3584

Regioselective electrophilic addition vs epoxidation of mCPBA towards anti-Bredt olefin of fulleroid

Author keywords

Anti Bredt olefin; Electrophilic addition to olefin; Fullerene; Oxidation

Indexed keywords

3 CHLOROPERBENZOIC ACID; ALKENE; CHEMICAL COMPOUND; FULLEROID; UNCLASSIFIED DRUG;

EID: 84861980010     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.05.007     Document Type: Article
Times cited : (9)

References (38)
  • 13
    • 0035802339 scopus 로고    scopus 로고
    • 3 lead to [5,6]-open fullerene oxide bearing high regioselectivity at the bridgehead, similar to the fulleroid. See
    • 3 lead to [5,6]-open fullerene oxide bearing high regioselectivity at the bridgehead, similar to the fulleroid. See: R.B. Weisman, D. Heymann, and S.M. Bachilo J. Am. Chem. Soc. 123 2001 9720 9721
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9720-9721
    • Weisman, R.B.1    Heymann, D.2    Bachilo, S.M.3
  • 21
    • 0029636783 scopus 로고
    • Such selective photooxygenation was also reported for azafulleroid. See
    • Such selective photooxygenation was also reported for azafulleroid. See: J.C. Hummelen, M. Prato, and F. Wudl J. Am. Chem. Soc 117 1995 7003 7004
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 7003-7004
    • Hummelen, J.C.1    Prato, M.2    Wudl, F.3
  • 30
    • 0033534553 scopus 로고    scopus 로고
    • A literature survey showed the reactions of some sterically strained olefins with mCPBA produce α-hydroxyl esters, although the mechanism was not discussed or featured to involve an epoxidation/acidic ring-opening sequence. See
    • A literature survey showed the reactions of some sterically strained olefins with mCPBA produce α-hydroxyl esters, although the mechanism was not discussed or featured to involve an epoxidation/acidic ring-opening sequence. See: T. Koerner, H. Slebocka-Tilk, and R.S. Brown J. Org. Chem. 64 1999 196 201
    • (1999) J. Org. Chem. , vol.64 , pp. 196-201
    • Koerner, T.1    Slebocka-Tilk, H.2    Brown, R.S.3
  • 37
    • 69549113131 scopus 로고    scopus 로고
    • Although our calculational method (DFT/B3LYP) is relatively rough as compared to the previous theoretical calculations (such as QCISD in Ref. 19a), these higher calculations cannot be straight forwardly applied to fulleroid with too many atoms and electrons. Multi-layered method such as ONIOM will enable such higher level calculation to fulleroid, as the following recent ONIOM application to the Diels-Alder reaction of fullerene. See
    • Although our calculational method (DFT/B3LYP) is relatively rough as compared to the previous theoretical calculations (such as QCISD in Ref. 19a), these higher calculations cannot be straight forwardly applied to fulleroid with too many atoms and electrons. Multi-layered method such as ONIOM will enable such higher level calculation to fulleroid, as the following recent ONIOM application to the Diels-Alder reaction of fullerene. See: S. Osuna, J. Morera, M. Cases, K. Morokuma, and M. Solà J. Phys. Chem. A 113 2009 9721 9726
    • (2009) J. Phys. Chem. A , vol.113 , pp. 9721-9726
    • Osuna, S.1    Morera, J.2    Cases, M.3    Morokuma, K.4    Solà, M.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.